Two Weeks in Italy: Food, Wine, Architecture & Adventure for Couples

Day 1: Arrival & Roman Charm

Rome, Italy on May 5, 2025

9:00am

Breakfast at Sant'Eustachio Il Caffè

Start the day with exquisite Italian coffee at this famous café known for its rich espresso, perfect for the coffee connoisseur husband.
EUR5, 1h0m

10:30am

Visit the Pantheon

Explore one of Rome's best-preserved architectural masterpieces with its iconic dome and ancient charm, ideal for lovers of architecture.
EUR0, 1h30m

12:30pm

Lunch at Roscioli

Enjoy an authentic Roman meal at Roscioli, a gourmet deli and restaurant offering delicious traditional dishes and local wines.
EUR35, 1h30m

2:30pm

Visit Trevi Fountain and Spanish Steps

Walk to these iconic landmarks to admire baroque architecture and romance, a perfect stroll through Roman charm.
EUR0, 1h0m

4:00pm

Chocolate tasting at Venchi

Indulge in artisanal Italian chocolates at Venchi, offering a variety of fine chocolates perfect for the chocolate-loving wife.
EUR15, 45m

7:30pm

Dinner at Trattoria Da Enzo al 29

Savor authentic Roman cuisine at this cozy trattoria famous for its carbonara and traditional ambiance.
EUR40, 2h0m
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Day 2: Historical Rome Tour

Rome, Italy on May 6, 2025

8:30am

Breakfast at Tazza d'Oro

Enjoy another coffee delight at this renowned café near the Pantheon, celebrating different espresso blends.
EUR6, 1h0m

9:30am

Colosseum & Roman Forum Tour

Explore the Colosseum’s grandeur and the Roman Forum’s ruins on a guided tour revealing Rome’s ancient history and architectural feats.
EUR18, 3h0m

1:00pm

Lunch at Mercato Centrale Roma

Visit the bustling food market offering diverse Italian street foods, perfect for discovering local flavors.
EUR25, 1h15m

2:30pm

Visit Vatican Museums & Sistine Chapel

See masterpieces of Renaissance art and architecture, including Michelangelo’s iconic ceiling in the Sistine Chapel.
EUR30, 3h0m

6:00pm

Chocolate gelato at Gelateria del Teatro

Experience decadent handmade gelato with rich chocolate flavors, perfect for an evening treat.
EUR7, 30m

7:30pm

Dinner at Osteria da Fortunata

Delight in handmade pasta and traditional Roman dishes in an intimate setting.
EUR45, 2h0m
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Day 3: Rome to Florence

Rome to Florence, Italy on May 7, 2025

7:30am

Early breakfast at Chocolat – Gelato al Cioccolato

Start the day with coffee and special chocolate treats combining favorites for both husband and wife.
EUR8, 45m

8:30am

Train from Rome to Florence

High-speed train journey (about 1.5 hours) offers comfortable and scenic travel to Florence.
EUR50, 1h30m

10:15am

Check-in and rest

Arrival in Florence and settle into your hotel located central to major attractions.
EUR0, 1h0m

11:30am

Lunch at Trattoria Mario

Enjoy traditional Tuscan cuisine at this beloved spot known for its hearty dishes.
EUR30, 1h15m

1:00pm

Visit Florence Cathedral and Baptistery

Admire the stunning Renaissance architecture of the Duomo complex, including Brunelleschi's dome.
EUR18, 1h30m

3:00pm

Coffee tasting at Ditta Artigianale

Explore artisan coffees curated by experts at this specialty coffee shop, ideal for the coffee-loving husband.
EUR10, 45m

4:00pm

Stroll along Ponte Vecchio & explore artisan shops

Walk the famous medieval bridge lined with jewelers, offering charming views and shopping.
EUR0, 1h0m

7:30pm

Dinner at La Giostra

Dine on refined Tuscan dishes in a cozy, romantic setting, popular among locals and visitors.
EUR50, 2h0m
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Day 4: Florence Art & Chocolate

Florence, Italy on May 8, 2025

8:30am

Breakfast at Rivoire

Start with rich cappuccinos and exquisite chocolates at this historic café in Piazza della Signoria.
EUR12, 1h0m

9:30am

Visit Uffizi Gallery

View world-renowned Renaissance masterpieces by Botticelli, Leonardo, and Michelangelo in a stunning palace.
EUR20, 3h0m

1:00pm

Lunch at Mercato Centrale Florence

Sample a variety of local foods and wines at this vibrant food hall with multiple artisan stalls.
EUR25, 1h0m

2:30pm

Visit Boboli Gardens

Explore the scenic gardens behind Pitti Palace with magnificent architecture, sculptures, and views over Florence.
EUR10, 2h0m

5:00pm

Chocolate tasting at Venchi Chocolate Boutique

Indulge in premium Italian chocolates and unique chocolate drinks by the wife’s favorite chocolatier.
EUR15, 45m

7:30pm

Dinner at Osteria Vini e Vecchi Sapori

Enjoy traditional Tuscan specialties paired with excellent regional wines in a cozy atmosphere.
EUR45, 2h0m
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Day 5: Horseback Riding Excursion

Tuscany Countryside near Florence, Italy on May 9, 2025

8:00am

Breakfast at hotel

Enjoy a relaxing breakfast before the day’s adventure.
Included, 1h0m

9:00am

Horseback Riding Tour in Chianti

Experience a 3-hour guided horseback ride through scenic Tuscan vineyards and hills, suitable for all experience levels.
EUR100, 3h0m

1:00pm

Lunch at Osteria Le Panzanelle

Savor authentic local cuisine near the riding area with fresh, seasonal dishes and Tuscan wine.
EUR35, 1h30m

3:00pm

Return to Florence and rest

Free afternoon to relax or explore Florence at leisure.
EUR0, 3h0m

6:30pm

Coffee sampling at La Ménagère

Indulge in specialty coffees and charming ambiance at this contemporary coffee-house and floral shop hybrid.
EUR10, 45m

8:00pm

Dinner at Il Santo Bevitore

Finish the day with innovative Tuscan cuisine and a great wine list in a stylish setting.
EUR50, 2h0m
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Day 6: Travel to Montepulciano

Montepulciano, Italy on May 10, 2025

8:00am

Breakfast at hotel in Florence

Have an early refreshing breakfast to prepare for the journey.
Included, 1h0m

9:30am

Drive to Montepulciano

A scenic 1.5-hour drive to Montepulciano, famous for its charming medieval streets and wine production.
EUR0, 1h30m

11:00am

Hotel check-in and explore town

Settle into your accommodation and start exploring the historic hilltop town, known for Renaissance palaces and panoramic views.
EUR0, 1h0m

12:00pm

Lunch at La Porta

Enjoy traditional Tuscan dishes and excellent wine in a quaint setting overlooking vineyards.
EUR40, 1h30m

2:00pm

Wine Tour & Tasting at Avignonesi Winery

Participate in a guided winery tour including tasting of renowned Vino Nobile di Montepulciano wines.
EUR45, 2h0m

5:00pm

Relax and visit local chocolate shop Caffè Poliziano

Sample local chocolates and enjoy a coffee at this historical café famous for its handcrafted sweets.
EUR15, 45m

7:30pm

Dinner at Osteria Acquacheta

Famous for its steak and rustic Tuscan flavors, offering an authentic local dining experience.
EUR45, 2h0m
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Day 7: Montepulciano Wine & Culture

Montepulciano, Italy on May 11, 2025

8:30am

Breakfast at your hotel

Enjoy a leisurely breakfast before the day’s discoveries.
Included, 1h0m

9:30am

Visit Montepulciano Cathedral and Piazza Grande

Explore the Renaissance cathedral and historic town square showcasing stunning architecture and great photo opportunities.
EUR0, 1h30m

11:30am

Coffee at Latte di Luna

A cozy spot offering specialty coffee perfect for the husband’s coffee interest.
EUR7, 45m

12:30pm

Lunch at Osteria Del Borgo

Enjoy refined Tuscan dishes paired with local wine in a charming medieval setting.
EUR40, 1h30m

2:30pm

Visit Cantina Contucci for Wine Tasting

One of the oldest wine cellars in town, offering deep insights into Montepulciano’s winemaking with tastings.
EUR35, 2h0m

5:00pm

Afternoon sweets at Casa de Vini

Enjoy traditional Tuscan biscuits and chocolates paired with coffee or wine.
EUR15, 45m

7:30pm

Dinner at La Grotta

A romantic cave-like restaurant serving classic dishes with a modern twist.
EUR50, 2h0m
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Day 8: Explore Venice

Venice, Italy on May 12, 2025

7:30am

Breakfast at hotel

Early breakfast before departure.
Included, 1h0m

8:30am

Drive/Train to Venice

Travel approximately 3.5 to 4 hours from Montepulciano to Venice by train or car transfer.
EUR60, 4h0m

12:30pm

Check-in and lunch at Osteria al Mascaron

Experience Venetian seafood specialties in a traditional, rustic venue near Rialto.
EUR40, 1h30m

2:00pm

Walk to St. Mark’s Square and Basilica

Visit iconic Venetian landmarks boasting stunning Byzantine architecture and lively atmosphere.
EUR5 (Basilica entry optional), 2h0m

5:30pm

Chocolate tasting at Venchi Venice

Indulge in premium chocolates and exclusive Venetian chocolate flavors.
EUR15, 30m

7:30pm

Dinner at Antiche Carampane

Enjoy classic Venetian dishes with fresh seafood prepared authentically.
EUR50, 2h0m
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Day 9: Venice & Gondola Ride

Venice, Italy on May 13, 2025

8:30am

Breakfast at Torrefazione Cannaregio

Specialty coffee and light pastries in a Venetian coffee roaster café perfect for coffee lovers.
EUR8, 1h0m

9:30am

Gondola Ride

Experience an iconic romantic gondola ride through Venice’s enchanting canals for about 30-40 minutes.
EUR80, 45m

10:30am

Visit Doge’s Palace

Explore the grand Gothic palace, its opulent rooms, and history of Venetian government and art.
EUR25, 2h0m

1:00pm

Lunch at Trattoria alla Madonna

Savor traditional Venetian cuisine with a focus on fresh seafood dishes.
EUR40, 1h30m

3:00pm

Visit Murano Island for Glass and Chocolate

Take a short boat trip to Murano to admire its glass craftsmanship and enjoy artisanal chocolates at local shops.
EUR15, 3h0m

7:00pm

Dinner at Osteria alle Testiere

Highly acclaimed seafood osteria serving fresh, innovative Venetian cuisine.
EUR55, 2h0m
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Day 10: Travel to Lake Como

Lake Como, Italy on May 14, 2025

7:30am

Breakfast at hotel

Enjoy a good breakfast before travel.
Included, 1h0m

8:30am

Train to Lake Como

Travel by train from Venice to Como (approximately 3.5-4 hours), enjoying beautiful northern Italy scenery.
EUR60, 4h0m

12:30pm

Check-in and lunch at Ristorante Villa d'Este

Dine in luxury with stunning views of Lake Como featuring refined Italian cuisine.
EUR50, 1h30m

2:00pm

Boat tour of Lake Como

Take a 2-hour scenic boat tour visiting towns like Bellagio and Varenna, enjoying lake views and architecture.
EUR25, 2h0m

5:00pm

Chocolate and coffee treat at Antica Pasticceria Confetteria L'Angolo della Dolcezza

Sample local chocolates and Italian coffee specialties.
EUR15, 45m

7:30pm

Dinner at Ristorante Mistral

Michelin-starred restaurant offering innovative dishes showcasing lake fish and local ingredients.
EUR80, 2h0m
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Day 11: Lake Como Exploration

Lake Como, Italy on May 15, 2025

8:00am

Breakfast at local café Caffè Monti

Start with freshly brewed coffee and pastries by the lake.
EUR8, 1h0m

9:30am

Visit Villa Carlotta and Gardens

Explore the beautiful villa and its botanical gardens, showcasing lush landscapes and lake views.
EUR15, 2h0m

12:00pm

Lunch at La Punta Spartivento

Relax with a meal offering spectacular panoramic lake views and regional dishes.
EUR40, 1h30m

2:00pm

Hike the Greenway del Lago di Como

Enjoy a scenic 3-4 hour walk along Lake Como’s historic path passing charming villages and architecture.
EUR0, 3h30m

6:00pm

Coffee and chocolate pairing at Pasticceria Poletti

Delight in an expertly paired session of Italian coffee and artisan chocolates.
EUR15, 45m

7:30pm

Dinner at Il Gatto Nero

Dine with lakeside views offering exquisite Italian cuisine and a romantic atmosphere.
EUR50, 2h0m
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Day 12: Departure Day

Lake Como, Italy on May 16, 2025

8:00am

Breakfast at hotel

Enjoy your final breakfast in Italy with lake views.
Included, 1h0m

9:30am

Leisurely morning walk around Como town

Take a relaxing stroll to revisit favorite spots or shop for souvenirs.
EUR0, 2h0m

12:00pm

Lunch at Osteria del Gallo

Enjoy a last traditional Italian meal featuring local lakeside specialties.
EUR40, 1h30m

2:00pm

Transfer to Milan Malpensa Airport

Travel to Milan airport (about 1.5 hours) for international departure.
EUR60, 1h30m
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